CN108484680B - Iridium complex with bis-thio aromatic ring/aromatic heterocyclic phosphoric acid compound as auxiliary ligand - Google Patents
Iridium complex with bis-thio aromatic ring/aromatic heterocyclic phosphoric acid compound as auxiliary ligand Download PDFInfo
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- CN108484680B CN108484680B CN201810099070.5A CN201810099070A CN108484680B CN 108484680 B CN108484680 B CN 108484680B CN 201810099070 A CN201810099070 A CN 201810099070A CN 108484680 B CN108484680 B CN 108484680B
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- 229910052741 iridium Inorganic materials 0.000 title claims abstract description 49
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 title claims abstract description 49
- 239000003446 ligand Substances 0.000 title abstract description 30
- -1 aromatic heterocyclic phosphoric acid compound Chemical class 0.000 title abstract description 14
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 title abstract description 12
- 229910000147 aluminium phosphate Inorganic materials 0.000 title abstract description 9
- 125000003118 aryl group Chemical group 0.000 title description 9
- 238000002360 preparation method Methods 0.000 claims description 8
- 239000000463 material Substances 0.000 abstract description 39
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 15
- 238000002347 injection Methods 0.000 abstract description 10
- 239000007924 injection Substances 0.000 abstract description 10
- 230000015572 biosynthetic process Effects 0.000 abstract description 8
- 238000003786 synthesis reaction Methods 0.000 abstract description 8
- 238000000859 sublimation Methods 0.000 abstract description 7
- 230000008022 sublimation Effects 0.000 abstract description 7
- 229910052717 sulfur Inorganic materials 0.000 abstract description 6
- 230000005540 biological transmission Effects 0.000 abstract description 4
- 238000000746 purification Methods 0.000 abstract description 4
- 230000001105 regulatory effect Effects 0.000 abstract description 4
- 239000011593 sulfur Substances 0.000 abstract description 4
- QCJQWJKKTGJDCM-UHFFFAOYSA-N [P].[S] Chemical group [P].[S] QCJQWJKKTGJDCM-UHFFFAOYSA-N 0.000 abstract description 3
- 230000009286 beneficial effect Effects 0.000 abstract description 3
- 239000000969 carrier Substances 0.000 abstract description 3
- 230000001276 controlling effect Effects 0.000 abstract description 3
- 238000005286 illumination Methods 0.000 abstract description 3
- 239000000126 substance Substances 0.000 abstract description 2
- 239000002131 composite material Substances 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 11
- 125000001072 heteroaryl group Chemical group 0.000 description 9
- 229910019142 PO4 Inorganic materials 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 7
- 239000010452 phosphate Substances 0.000 description 7
- 125000004076 pyridyl group Chemical group 0.000 description 7
- 125000000714 pyrimidinyl group Chemical group 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical group C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 125000002098 pyridazinyl group Chemical group 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 125000004306 triazinyl group Chemical group 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 3
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Chemical group COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000002061 vacuum sublimation Methods 0.000 description 3
- RKVIAZWOECXCCM-UHFFFAOYSA-N 2-carbazol-9-yl-n,n-diphenylaniline Chemical compound C1=CC=CC=C1N(C=1C(=CC=CC=1)N1C2=CC=CC=C2C2=CC=CC=C21)C1=CC=CC=C1 RKVIAZWOECXCCM-UHFFFAOYSA-N 0.000 description 2
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 2
- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 description 2
- YWKKLBATUCJUHI-UHFFFAOYSA-N 4-methyl-n-(4-methylphenyl)-n-phenylaniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(C)=CC=1)C1=CC=CC=C1 YWKKLBATUCJUHI-UHFFFAOYSA-N 0.000 description 2
- ZOKIJILZFXPFTO-UHFFFAOYSA-N 4-methyl-n-[4-[1-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1(CCCCC1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZOKIJILZFXPFTO-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 2
- 229910021638 Iridium(III) chloride Inorganic materials 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical group C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000001194 electroluminescence spectrum Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 230000005525 hole transport Effects 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical group [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 150000002503 iridium Chemical class 0.000 description 2
- 125000005956 isoquinolyl group Chemical group 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- JLXXLCJERIYMQG-UHFFFAOYSA-N phenylcyanamide Chemical compound N#CNC1=CC=CC=C1 JLXXLCJERIYMQG-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 125000005493 quinolyl group Chemical group 0.000 description 2
- 230000006798 recombination Effects 0.000 description 2
- 238000005215 recombination Methods 0.000 description 2
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical group C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000003943 azolyl group Chemical group 0.000 description 1
- 150000001555 benzenes Chemical group 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- XGRJZXREYAXTGV-UHFFFAOYSA-N chlorodiphenylphosphine Chemical compound C=1C=CC=CC=1P(Cl)C1=CC=CC=C1 XGRJZXREYAXTGV-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000011365 complex material Substances 0.000 description 1
- 239000008358 core component Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000007772 electrode material Substances 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229930192474 thiophene Chemical group 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
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- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
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Abstract
The invention relates to a novel iridium complex which takes nitrogen heterocycle as a main ligand and takes a double-sulfur aromatic ring/aromatic heterocycle phosphoric acid compound as an auxiliary ligand. Nitrogen heterocycles and phosphorus-sulfur groups in iridium complex molecules are beneficial to improving the electron mobility of the material and regulating and controlling the luminescent color, so that the injection and transmission of holes and electrons are balanced, the composite area of carriers is widened, the device efficiency is improved, and the efficiency roll-off is reduced. The iridium complex has the advantages of simple synthesis, stable chemical property, easy sublimation and purification, and excellent device performance, and provides convenience for obtaining high-efficiency organic electroluminescent devices and application thereof in the fields of illumination and display.
Description
Technical Field
The invention relates to the technical field of organic electroluminescent devices, in particular to an iridium complex luminescent material taking a bis-thio aromatic ring/aromatic heterocyclic phosphoric acid compound as an auxiliary ligand and an electroluminescent device applying the material.
Background
Under the large background of increasing global energy demand and great ecological environment worries, governments of various countries continuously and vigorously develop sustainable energy-saving technologies and industries based on high technology. An Organic Light-emitting Diode (OLED), also called an Organic Light-emitting Diode, is a device for converting electric energy into Light energy by applying a voltage thereto. Since the Duncuo cloud of Kodak corporation published the OLED with low voltage starting, high efficiency and high brightness, small molecule organic thin film double-layer structure in 1987, the research of electroluminescent materials and devices has attracted great interest in the world science and technology field and the industry. The OLEDs are flat panel display technologies with low power consumption, wide viewing angle, large area, and soft screen implementation, and are widely considered as the next generation of ideal display screens capable of replacing liquid crystal LCDs, inorganic LEDs, and the like, and being used in mobile phones, color tvs, and the like, and show attractive prospects in solid state lighting and flat panel display.
The unique advantages of OLEDs are closely related to the carrier transporting materials, light emitting materials, electrode materials, and the structure of the devices in which the light emitting materials are the core components of the OLEDs. The Ir (III) complex is a typical MLCT luminescent complex, has the advantages of good thermal stability, relatively short excited state life, high luminescent efficiency, easy adjustment of luminescent color and the like, and becomes a research hotspot in the field of electroluminescent materials.
It is known that the hole mobility of the hole layer is much greater than the electron mobility of the electron layer, which results in carrier imbalance and reduced device efficiency. Therefore, if the developed iridium complex luminescent material has good electron transmission performance, the transmission of carriers can be balanced, the carrier recombination region is widened, the efficiency of the device is improved, and the iridium complex luminescent material has important research significance for improving the performance of the device. In addition, the synthesis yield and sublimation purification yield of the complex for practical materials are critical to reduce the manufacturing cost of materials and devices. Therefore, it is necessary to provide an iridium complex light-emitting material having both high electron mobility and high synthesis and sublimation yield.
Disclosure of Invention
Aiming at the defects of the prior art, the invention designs a novel iridium complex containing a nitrogen heterocyclic ring main ligand and a bis-thio aromatic ring/aromatic heterocyclic ring phosphate compound auxiliary ligand and applies the material to an organic electroluminescent device. The nitrogen heterocyclic main ligand of the iridium complex can effectively improve the electron mobility of the complex, and the sulfur atom S has larger radius than oxygen, is easy to deform, has stronger coordination capacity with the iridium atom than oxygen, and has obvious improvement effect on the synthesis and sublimation yield of the complex.
The specific technical scheme of the invention is as follows:
an iridium complex takes nitrogen heterocycle with a C ^ N structure as a main ligand and takes a double-sulfur aromatic ring/aromatic heterocycle phosphoric acid compound as an auxiliary ligand, and the iridium complex has the following structure:
wherein the nitrogen heterocyclic main ligand can adopt any commonly used ligand with a C ^ N structure in iridium complex materials with various luminescent colors at present,
the group coordinated by the C segment is substituted or non-substituted phenyl, pyridyl or pyrimidyl; the N-segment coordinating group is substituted or unsubstituted pyridyl, pyrimidyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl or pteridinyl;
the auxiliary ligand is bisthio aromatic ring/heteroaromatic phosphoric acid, wherein R represents substituted or unsubstituted benzene or heteroaromatic ring, preferably phenyl, naphthyl, furyl, thienyl, pyridyl, pyrimidyl, pyridazinyl, triazinyl, pyrrolyl or azolyl, and preferably, R is substituted by H, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 halogenated alkyl and halogen elements at any position. More preferably R represents
In a preferred embodiment of the present invention, the bis-thio aromatic ring/aromatic heterocyclic phosphate compound is selected from the group consisting of:
the iridium complex of the inventionThe C-segment coordination group of the main nitrogen heterocyclic ligand can be selected from phenyl, pyridyl or pyrimidyl which is substituted by one or more of alkyl of H, C1-C6, alkoxy of C1-C6, halogenated alkyl of C1-C6, halogen elements, cyano, aniline and carbazole at any position. Preferably phenyl, pyridyl, thienyl or pyrimidyl which are substituted by one or more of H, methyl, methoxy, tert-butyl, fluorine, trifluoromethyl, cyano, aniline and carbazole at any position. More preferably, the C-segment coordinated group of the main nitrogen heterocyclic ligand is selected from
According to the iridium complex, a group coordinated by the N segment of the nitrogen heterocyclic main ligand is selected from pyridyl, pyrimidyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl or pteridinyl which are substituted by one or more of alkyl of H, C1-C6, halogenated hydrocarbon of C1-C6 and halogen elements at any position. Pyridyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl or pteridinyl substituted in any position by H, methyl, fluoro, trifluoromethyl are preferred. More preferably, the N-segment coordinated group of the main nitrogen heterocyclic ligand is selected from
In a preferred embodiment of the present invention, the main nitrogen heterocyclic ligand is selected from
In a preferred embodiment of the present invention, the iridium complex is selected from:
the bis-thio aromatic ring/heteroaromatic ring phosphate compound can be purchased commercially or prepared by the following method: refluxing bromo-aromatic ring/heteroaromatic ring and phosphorus trichloride in toluene under anaerobic condition for two hours, cooling, separating by column chromatography to obtain diaryl ring/heteroaromatic ring based phosphorus chloride, refluxing with sulfur powder in toluene under anaerobic condition for two hours, and stirring in sodium hydrosulfide aqueous solution for two hours to obtain sodium salt aqueous solution of the double-thio-aromatic ring/heteroaromatic ring phosphate compound. The definition of the aromatic ring/aromatic heterocycle is as described above, such as benzene, naphthalene, furan, thiophene, pyridine, pyrimidine, pyridazine, triazine, pyrrole or azole substituted by one or more of halogenated alkyl of H, C1-C6, halogen elements and carbazole at any position.
The iridium complexes of the invention may be prepared by conventional methods, for example by reacting a primary ligand with IrCl3Refluxing in an ethoxy ethanol solution for 10 hours in a ratio of 2:1, cooling and filtering to obtain an iridium chloro-bridge complex; then mixing the iridium chlorine bridge complex and the sodium salt water solution of the double-sulfur aromatic ring/heteroaromatic ring phosphate compound in a ratio of 1:2, refluxing for two hours in ethoxyethanol to obtain a crude product of the iridium complex, performing column chromatography to obtain a pure product, and further performing sublimation purification under a vacuum condition to obtain the luminescent material meeting the requirements of a preparation device.
The invention also aims to provide application of the iridium complex in preparing organic electroluminescent devices.
The iridium complex can be used for preparing an organic electroluminescent device, for example, the organic electroluminescent device comprises a substrate, an anode, a hole injection material, a hole transport layer, an organic luminescent layer, an electron transport layer, an electron injection material and a cathode. The substrate is glass, the anode is indium tin oxide, the hole injection layer is 2,3,6,7,10, 11-hexacyano-1, 4,5,8,9, 12-hexaazatriphenylene HAT-CN, the hole layer is made of 4,4' -cyclohexyl bis [ N, N-bis (4-methylphenyl) aniline TAPC material, the electron transport layer is made of 1,3, 5-tris [ (3-pyridyl) -3-phenyl ] benzene TmPyPb, the electron injection material is LiF, and the cathode is metal Al; the organic light-emitting layer comprises a main material and a light-emitting material, wherein the main material is 4,4' -tri (9-carbazolyl) triphenylamine TCTA, and the light-emitting material is the iridium complex.
The invention has the beneficial effects that: the iridium complex provided by the invention has the characteristics of high electron mobility, easy synthesis, stable chemical property and easy sublimation and purification. The preparation method of the material is simple and has high yield. Due to the introduction of nitrogen heterocyclic ring and phosphorus-sulfur bond, the comprehensive photoelectric property of the material can be effectively regulated and controlled, and convenience is provided for obtaining a high-efficiency organic electroluminescent device and application thereof in the fields of illumination and display.
Nitrogen heterocyclic rings and phosphorus-sulfur groups in the iridium complex molecules are good electron transport groups, and the introduction of the nitrogen heterocyclic rings and the phosphorus-sulfur groups is beneficial to improving the electron mobility of the material and regulating and controlling the luminescent color. Therefore, injection and transmission of holes and electrons are balanced, a recombination region of current carriers is widened, the efficiency of the device is improved, and the efficiency roll-off is reduced. For example, the performance of the device prepared by using the iridium complex SSdpp 1 as the luminescent center is far better than that of the device prepared by using the iridium complex with the same main ligand and the same auxiliary ligand as non-thiopyridine phosphate as the luminescent center [ see the literature: zheng-guard Wu, Yi-Ming Ju, guard-Zhao Lu, Jie Zhou, You-Xuan Zheng, Liang Zhou, Yi Wang, Jig-Lin Zuo, Yi Pan, Hong-Jie Zhang, Novel Design of Iridium Phosphors with pyridine Phosphors Ligands for high hly efficiency Blue Organic Light-emitting Diodes, Sci.Rep 478, 2016,6,38478.DOI:10.1038/srep38478 ]. And because the radius of the sulfur atom is larger than that of oxygen, the deformability is large, the combination with the transition metal iridium is firmer, and the synthesis yield and the vacuum sublimation yield are higher. The synthesis yield of the iridium complex is generally higher than 90%, the vacuum sublimation rate is also higher than 90%, and the synthesis yield is far higher than that (< 70%) and vacuum sublimation rate (< 60%) of most iridium complexes at present, so that the iridium complex is very suitable for industrial production.
Drawings
FIG. 1 shows an electroluminescence spectrum of an iridium complex SSdpp 1 used in an organic electroluminescent device.
FIG. 2 is a graph showing the luminance and voltage curves of the iridium complex SSdpp 1 used in the organic electroluminescent device according to the present invention.
Fig. 3 is a current efficiency and luminance curve of the iridium complex SSdpp 1 provided by the present invention for use in an organic electroluminescent device.
Detailed Description
The following examples illustrate specific steps of the present invention, but are not intended to limit the invention.
Terms used in the present invention generally have meanings commonly understood by those of ordinary skill in the art, unless otherwise specified.
The present invention is described in further detail below with reference to specific examples and with reference to the data. It will be understood that this example is intended to illustrate the invention and not to limit the scope of the invention in any way.
In the following examples, various procedures and methods not described in detail are conventional methods well known in the art.
The present invention is further illustrated by the following specific examples.
EXAMPLE 1 preparation of an aqueous solution of sodium Bithiodiphenyl phosphate as an ancillary ligand
Refluxing bromobenzene and phosphorus trichloride (2:1) in toluene under anaerobic condition for two hours, cooling, separating by column chromatography to obtain diphenyl phosphorus chloride, refluxing with sulfur powder in toluene under anaerobic condition for two hours, stirring in sodium hydrosulfide aqueous solution for two hours to obtain sodium bisulphodiphenylphosphonate aqueous solution
The yield reaches 100 percent.
The aqueous solution of sodium salt of other double-sulfur aromatic ring/heteroaromatic ring phosphate compounds can be prepared by the method:
example 2 preparation of an Iridium Complex according to the invention
The main ligands 2-phenylpyridine and IrCl3Refluxing in an ethoxy ethanol solution for 10 hours in a ratio of 2:1, cooling and filtering to obtain an iridium chloro-bridge complex; then, 10mmol (10.72 g) of the chloro-bridged complex and 20mmol of an aqueous solution of sodium disulfobenzylphenylphosphate were refluxed in ethoxyethanol for two hours to give a crude product of the iridium complex, and column chromatography gave 13.80 g of pure SSdpp 1 (yield: 92%). And further 5 grams of SSdpp 1 were placed in a quartz tube at 10-5Heating, sublimating and purifying under the vacuum condition to obtain 4.7 g of luminescent material (sublimation rate is 94%) meeting the requirements of preparing devices. The reaction is shown below:
the obtained iridium complex SSdpp 1 is analyzed by nuclear magnetic resonance hydrogen spectrum and high-resolution mass spectrum as follows:
1H NMR(400MHz,CDCl3)8.56(d,2H),8.16(t,J＝7.4Hz,2H),7.82(d,J＝4.3Hz,2H),7.52-7.45(m,10H),7.42–7.15(m,14H),6.95(s,2H)。
HRMS(ESI)m/z calcd for C44H32Cl2Ir2N4[M+H]:1072.1020,found:1072.1017.
with reference to the above method, different primary ligands are selected:
and the thioaromatic ring/heteroaromatic ring phosphoric acid compound prepared in example 1 to obtain the following compounds:
example 3 preparation of Iridium Complex SSdpp 1 organic electroluminescent device
The preparation of the organic electroluminescent device of the present invention will be described below by taking SSdpp 1 as an example of the preparation of the organic electroluminescent device as the luminescent center of the luminescent layer. The structure of the OLEDs device includes: a substrate, an anode, a hole injection material, a hole transport layer, an organic light emitting layer, an electron transport layer, an electron injection material, and a cathode. The substrate is glass, the anode is indium tin oxide, the hole injection layer is 2,3,6,7,10, 11-hexacyano-1, 4,5,8,9, 12-hexaazatriphenylene HAT-CN (5nm), and the evaporation rate is 0.05 nm/s; the hole layer adopts 4,4' -cyclohexyl di [ N, N-di (4-methylphenyl) aniline TAPC material (50nm), and the evaporation rate is 0.05 nm/s; the electron transport layer adopts 1,3, 5-tri [ (3-pyridyl) -3-phenyl ] benzene TmPyPb (50nm), and the evaporation rate is 0.05 nm/s; the electron injection material is LiF (1nm), and the evaporation rate is 0.01 nm/s; the cathode is metal Al (100nm), and the evaporation rate is 0.2 nm/s; the organic light-emitting layer is of a doped structure, the thickness of the organic light-emitting layer is 40nm, the organic light-emitting layer comprises a main material and a light-emitting material, the main material is 4,4' -tris (9-carbazolyl) triphenylamine TCTA, the light-emitting material is an iridium complex, and the mass fraction of the iridium complex is 8 wt%.
Several materials used in the present invention have the following structure:
the invention selects a new iridium complex SSdpp 1 as a luminescent center to prepare an organic electroluminescent device. Referring to fig. 1, fig. 2 and fig. 3 together, fig. 1 shows an electroluminescence spectrum of the SSdpp 1 provided by the present invention for the organic electroluminescent device, and fig. 2 and fig. 3 show a photoelectric performance of the SSdpp 1 provided by the present invention for the organic electroluminescent device. As shown in FIGS. 2 and 3, the organic electroluminescent device had a starting voltage of 3.4V and a maximum luminance of 124000cd/m2The maximum current efficiency is 104.34cd/A, at 1000cd/m2The current efficiency can still be maintained at 93.12cd/a at luminance, showing a very small efficiency roll-off. The performance of the material is far superior to that of a device prepared by taking an iridium complex with the same main ligand and an auxiliary ligand as non-thiopyridine phosphoric acid as a luminescent center [ the maximum device brightness is 31270cd/m2The maximum current efficiency is 58.78cd/A, see literature: zheng-guard Wu, Yi-Ming Ju, guard-Zhao Lu, Jie Zhou, You-Xuan Zheng, Liang Zhou, Yi Wang, Jig-Lin Zuo, Yi Pan, Hong-Jie Zhang, Novel Design of Iridium Phosphors with pyridine Phosphors Ligands for high hly efficiency Blue Organic Light-emitting Diodes, Sci.Rep 478, 2016,6,38478.DOI:10.1038/srep38478.]. Research on photophysical properties shows that the iridium complex luminescent material containing the nitrogen heterocyclic main ligand and the bis-thio aromatic ring/aromatic heterocyclic phosphoric acid auxiliary ligand has higher device efficiency and has practical application value in the fields of display, illumination and the like.
The iridium complex SSdpp 2-68 prepared in the embodiment 2 of the invention can be prepared into an organic electroluminescent device by adopting the method, and has photoelectric properties similar to those of SSdpp 1.
The iridium complex provided by the invention can be used as a luminescent material to be applied to a luminescent layer of OLEDs, and the purpose of regulating and controlling the efficiency of a device is achieved by designing and optimizing the structure of a compound.
While the foregoing is directed to embodiments of the present invention, it will be understood by those skilled in the art that various changes may be made without departing from the spirit and scope of the invention.
Claims (2)
1. An iridium complex is characterized by having the following structure:
2. use of an iridium complex as claimed in claim 1 in the preparation of an organic electroluminescent device.
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